Don't Mess with Jenny

by Ashley Miller

 

Part 1: Now

"Hurry up Ash, your date will be here in a half-hour," Jenny called from downstairs. I sighed and continued putting on my foundation. His name was Paul, and we had met him at a dance club downtown. Naturally, Jenny had wasted no time in introducing us. I had to bite back the urge to mutter a curse at the woman, but she had trained me well as you will soon discover. "Thanks," I yelled back. "I'm so excited!"

I finished putting my basecoat on and got to work contouring. I have a naturally round face, so I need a little help from MAC to pass. I have to admit, I've gotten quite good with makeup application. Jenny had certainly made sure that I had gotten plenty of practice. I set to work blending using a headband to keep from getting any makeup in my platinum blond pageboy which had been freshly highlighted that afternoon. By now the girls at the salon had gotten used to me and I wasn't quite the spectacle I was at the beginning. They thought of me less like a sideshow and more like a sister.

I lined my lips in a light shade and set about applying a pretty shade of light pink on my lips. Almost without thinking I grabbed a piece of TP and pressed it against my lips, smooching down and then re-applying the feminine shade. I tossed the lipstick tube onto the bed to make sure that I remembered to put it in my purse for the night and set to work on my eyes.

Eye shadow and liner have always been the most difficult for me. Mascara is a snap, but I have a phobia about getting things in my eyes and I had a hell of a time mastering them. When we first got started, Jenny applied my makeup for me. Now, I have plenty of regrets for EVER allowing her to do that. This had all started out so innocently, but looking back I realize that I have nobody to blame but myself for the situation I'm in.

I removed the headband and primped my hair a bit more. I looked pretty good, certainly much better than I had when we started. I wasn't going to make the cover of Maxim but I was more than passable as a woman. It was now time to get dressed, and despite all that had happened I still got excited over that part.

The usual foundation garments that a girl like me needs gave me the proper feminine hourglass shape. I still wear a corset although with Jenny's rigorous exercise schedule I could probably go without it. But it does provide the hourglass shape that really sells the illusion, so it's worth the trouble to me.

I chose my favorite satin bra/panty combo in a pretty shade of pink and put them on. My bra and panties always match, and I wear nothing but stuff from Secret. The full-coverage bra was MADE for us girls! I placed a "C" breast form in each cup and returned to the bathroom. With some creative use of more foundation and shadow I quickly had passable cleavage. The forms were some of the first items that Jenny had forced me to purchase with my credit card. I had resisted at first, saying that we could fill them with anything. When we first started we had used five dollar napkins for God's sake! But she insisted and had me over a barrel. And in the end, it turned out that I kind of like the forms after all.

I rolled the pantyhose up each leg, being extra careful to not get any runs. My freshly-shaven legs looked wonderful in them. When I still lived life as a man, I was told by a lot of women that I had great legs. Of course, they had hair on them back then. If those girls could see me now! Next I put on a pretty gold lame sleeveless shell top that zipped and buttoned up the back. I had searched relentlessly over the Internet for a top like this. Back when I was just a little boy who was confused over his desire to wear women's clothing I had seen a top like this in a Sears catalog. This one wasn't exactly like that one, but it was a reasonable facsimile. I finished off my outfit by zipping up my Jones New York leather skirt and straightening it. I checked myself out in the full-length mirror on the back of my bedroom door. I looked pretty damn good!

After putting on my favorite ankle-high PVC boots, I click-click-clicked down the stairs. Jenny was sitting in the kitchen making dinner for her the man who replaced me as her boyfriend. Upon hearing me, she quickly turned around. "You look hot Ashley," she said with a wide smile. "I'm guessing that John and I shouldn't wait up!" She dropped me a wink as I cringed a little, but likely enough for her to notice. The only think Jenny loved more than feminizing me was bringing up John and seeing my reaction. I always wished that I could hide it better.

Right about now you're likely wondering exactly how I came to be in this predicament. Like I mentioned before, it is entirely my own fault. As you will come to see I was a bit of a pig with a considerable secret that I revealed to the wrong person. And then I pissed her off. What follows is an account of how Jenny Anderson exacted her revenge upon me. What follows is what happened when I messed with Jenny!

  

  

  

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